Carbohydrates: Structure & Biological Function

(Chapter 7)
™Carbohydrates are the most abundant class of biomolecules. They play a
role in energy metabolism and storage, they are building blocks of
polysaccharides, nucleic acids & glycoproteins, they provide structural
scaffolding for cell walls, and they are involved in molecular recognition.
™Characteristics of carbohydrates: one or more chiral centers, linear and
ring structures, polymeric structures via glycosidic bonds, & extensive
hydrogen bonding.
7.1 Monosaccharides
-simple carbohydrates (CH2O)n (where n is 3 to 7) that serve as building
blocks (monomers) of more complex carbohydrates (polysaccharides)
-aldoses contain an aldehyde & ketoses contain a ketone
-Fischer projections represent the linear form of monosaccharides
7.2 Carbohydrates in Cyclic Structures
-the cyclic form of monosaccharides is favored over the linear form in soln
-furanoses are five-membered rings & pyranoses are six-membered rings
-Haworth projections represent the cyclic form of monosaccharides
-anomers (α & β) differ in stereochemistry at the anomeric carbon
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Carbohydrates: Structure & Biological Function

(Chapter 7) – Cont.
7.3 Reactions of Monosaccharides
-monosaccharides form disaccharides by forming an O-glycosidic bond
-important disaccharides include sucrose, lactose, cellobiose & maltose
-nomenclature of glycosidic bonds (linkages)
7.4 Polysaccharides
-oligosaccharides contain 3 – 10 monosaccharide units.
-polysaccharides contains more than 10 monosaccharide units.
-Important storage polysaccharides include starch (amylose and
amylopectin) and glycogen
-Important structural polysaccharides include cellulose & chitin
7.5 Glycoproteins
-proteins that have covalently attached carbohydrate units & are involved in
immunity, cell-cell recognition, blood clotting & signal transduction
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7.1 Monosaccharides
Learning Objectives: understand the fundamental structures, group classification &
stereochemistry of the monosaccharides
™Aldoses contain an aldehyde at carbon 1

™Ketoses contain a ketone at carbon 2

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Aldoses
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Ketoses

™EXAMPLE: Glucose is an:

a) Aldopentose
b) Ketopentose
c) Aldohexose
d) Ketohexose
™EXAMPLE: Fructose is an:
a) Aldopentose
b) Ketopentose
c) Aldohexose
d) Ketohexose
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7.2 Carbohydrates in Cyclic Structures

Learning Objectives: be able to show the cyclization of monosaccharides to form
pyranoses & furanoses
™In aqueous solution, carbohydrates form cyclic structures with creation
of an additional asymmetric chiral carbon (carbon 1, anomeric carbon)
™Aldohexoses form pyranose (6-membered) rings
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Carbohydrates in Cyclic Structures – Cont.

™Ketohexoses form furanose (5-membered) rings

™EXAMPLE: Circle the anomeric carbon in the two Haworth projections above
for fructose & for glucose on the previous page.
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7.3 Reactions of Carbohydrates

Learning Objectives: know the fundamental reaction to form disaccharides
™Disaccharides & polysaccharides contain O-glycosidic bonds
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Disaccharides

Reducing End –

Nonreducing End –

™EXAMPLE: What is the only nonreducing disaccharide on the previous page?

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7.4 Polysaccharides
Learning Objectives: be able to recognize the structures & functions of polysaccharides
™Characterization of Polysaccharides
-the identity of the monomeric units
-the sequence of monosaccharide residues
-types of glycosidic bond linking the units
-approximate length (number of monosaccharides) of the chain
-degree of branching

™Biological Functions of Polysaccharides

-Storage: Starch

Glycogen

-Structure: Cellulose

Chitin

-Bacterial Cell Wall: Peptidoglycan

-Recognition: Cell Surface Polysaccharides

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Starch (α-Amylose & Amylopectin) & Glycogen

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Cellulose & Chitin (Structural Polysaccharides)

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Summary of the Structures & Properties of Common

Polysaccharides
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7.5 Glycoproteins
Learning Objectives: describe the structure & function of glycoproteins
™Glycoproteins have covalently bonded carbohydrate units attached via
amino acid side chains

™EXAMPLE: What are the general functions of glycoproteins. Provide some

specific examples.